2 Chieftain Crescent, Toronto, ON
St. Andrew-Windfields, Toronto · MLS® C12812110
About this home
A Spectacular Showcase Oversized Corner Lot For Your Own Creation, OR, Regenerate This Sprawling Custom-Built 4 Bedroom To Be Once Again A Real Gem. A Majestic Property In The Heart Of Fifeshire. A Prominent Toronto Builder's Family Home Since 1966 With Over 5,000 Sq.Ft. Of Living Space. The Main Floor Rooms Have Abundant Daylight In An Intelligently Designed Floor Plan. A Central Family Room Features Heritage Wood Moldings Taken From The Old Chorley Park Mansion Of Toronto. Walkout To The Pool. Large Living and Dining Rooms Are Accessed From The Stately Grand Hall Entrance. Upstairs Are 4 Bedrooms. The Corner Lot With Picturesque And Appealing Landscaping Is An Above Average Size Of 107' x 150' **EXTRAS** Extra Carved Wooden Mouldings in the Basement From The Demolition Old Chorley Park Mansion.
Key facts
- Property type
- Detached, 2-Storey
- MLS®
- C12812110
- Bedrooms
- 5 (4 + 1)
- Bathrooms
- 5 (2 half)
- Size
- 3500-5000
- Lot
- 107.41 × 150.71 ft
- Cross streets
- Fifeshire and Bayview
- Parking
- 2 garage · 4 parking (attached)
- Driveway
- Private Double
- Basement
- Finished, Full
- Kitchens
- 2 (1 + 1)
- Heating
- Forced Air
- A/C
- Central Air
- Exterior
- Shingle
- Foundation
- Poured Concrete
- Roof
- Cedar, Shake
- Sewer
- Sewer
- Pool
- Inground
- Property tax
- $16,858 / 2026
- Days on market
- 144
- Listing brokerage
- ROYAL LEPAGE TERREQUITY REALTY
Rooms
Listed at $4,050,000, this home is within the range of comparable homes, on the lower side. The number above is my independent estimate of value, not the asking price.
Based on 11 similar homes nearby, adjusted for size, beds, and baths.Median of 11 comparable active listings, adjusted for size, beds, and baths. The city (MPAC) assessment points to about $3.19M, lower than the comparables and worth a second look.
How I got there
Here is the exact math behind the estimate. I start from the closest comparable listing and adjust for the real differences (size, beds, baths) to land on a like-for-like value for this home.
- Closest comparable, listed at $5.00M
- Bathrooms −$15K
- Adjusts to $4.98M
That comparable adjusts to $4.98M; the $4.39M estimate above is the median of all 11 comparables, which is steadier than any single home.This uses comparable active listings, not sold prices. Lot, condition, and finishes are my in-person call, and I can run a full CMA with recent solds.
On schools, this address is zoned for York Mills Collegiate Institute, one of the higher-rated public schools in the area. A strong catchment tends to hold value and widen your resale pool, especially with family buyers.
On location, it is moderately walkable, so some daily errands are within reach and for the rest you will likely drive. Toba Dr at Fifeshire Rd is about a 1-minute walk away.
Total price vs nearby homes. Fair value about $4.39M, median of 11 comparables.
What the listing highlightsThese are claims from the listing. The only way to know for sure is to see it in person, and I am happy to book you a private showing.
- Pool: lifestyle appeal, but adds maintenance, insurance, and resale is mixed.
- Corner lot: more light and frontage, sometimes at the cost of privacy.
- Weigh carefully
The closest active listings by size, beds, and price, so you can see what this home is up against.
The 5 closest of 8 active listings nearby.
See all comparable homesThis home lists 3% below the area average of $985/sqft.
143 days longer than the Toronto average (1 days).
View comparable listingsPrice per square foot vs the area average.
Neighbourhood & location
St. Andrew-Windfields, Toronto, ON
Enter a workplace or destination and we’ll show the door-to-door time by car, transit and bike.
Getting around
WalkableA walkability read built from the amenities around this home: how close the nearest transit stop is, and how many grocery, dining, park, and pharmacy destinations fall within a 15-minute walk. It is a guide, not a guarantee. Places data from Google.
Many errands can be done on foot; a car still helps.
🚉 Nearest transit: Toba Dr at Fifeshire Rd, about 108 m away
Within a 15-minute (1.5 km) walk.
How asking prices compare in the closest areas to this home. Longer bars mean a pricier market.
Typical asking price of active listings of the same type, per area (outliers removed). Toronto.
Get the full neighbourhood report (schools, parks, transit & safety) →
The public and Catholic schools this address is zoned for, with EQAO results (the share of students meeting Ontario's provincial standard).
School attendance boundaries and EQAO results are Ontario government data and can change. Confirm the current catchment with the school board before relying on it.
Affordability & Mortgage
Income needed assumes a ~32% GDS ratio; weekly is mortgage principal & interest only. Price ÷ income is the home price over the income needed. Fixed reference assumptions so listings compare on equal footing, not a lending decision.
Calculate and customize your mortgage and other expenses
Adjust the down payment, rate, and amortization, and add property tax, condo fees, and heating to see your true monthly cost.
Your numbers
Homes over $1.5M can't be insured, so 20% down or more is required.
Conventional (20%+ down). Best insured 5-year fixed 3.99% via Ratehub.ca (as of July 17, 2026); conventional rates run a little higher.
Mortgage amount $3,240,000 · 4.14% over 25 years
Total monthly cost
- Mortgage payment (monthly equivalent)
- $17,290
- Property tax
- $1,405
- Condo / maintenance fees
- $0
- Heating
- $0
- Estimated monthly cost
- $18,695
Add your own property tax, condo fees, and heating on the left for a sharper total.
One-time closing costs
- Ontario land transfer tax
- $87,725
- Toronto municipal land transfer tax
- $98,725
- Estimated closing costs
- $186,450
Plus your down payment of $810,000. Legal fees, title insurance, and adjustments are extra and vary by deal.
Mortgage stress test
Lenders qualify you at the greater of your rate plus 2% or 5.25%. You do not pay this rate. It just shows you could still handle payments if rates rose, so aim to stay comfortable at this higher number.
Over the full 25 years
At the end of your 5-year term
- Total paid over the term
- $1,037,391
- Principal paid down
- $412,615
- Interest paid
- $624,776
- Balance remaining
- $2,827,385
Talk to Team Asgarian about your options
Rates and programs change often. We will connect you with a trusted mortgage professional and build a plan that fits your budget and goals.
Estimates only, not a mortgage quote or pre-approval. Figures use Canadian semi-annual compounding, current minimum down-payment rules, CMHC premium tiers, and Ontario (plus Toronto, when selected) land transfer tax. Actual rates, taxes, insurance, and closing costs vary by lender and property. Confirm every number with your mortgage professional.
Investor snapshot
Thinking of this home as an investment? We will pull real comparable rents and run the full numbers with you.
Talk about the numbersEstimates only. Rent is modelled on above-grade size and local norms, so a finished basement or second suite (a separate entrance often means one) can push real rent well above this. Taxes, fees, and vacancy vary by property, and cap rate is before financing. A starting point, not a final number, let us run the real ones with you.
Helpful resources
All information deemed reliable but not guaranteed. For personal, non-commercial use only. Listing courtesy of ROYAL LEPAGE TERREQUITY REALTY. MLS®/PropTx.